Month: February 2023

4-Amino-6-(piperidin-1-yl)pyrimidine-5-carbonitrile was written by Bhat, Radhika;Shraddha, K. N.;Begum, Noor Shahina. And the article was included in IUCrData in 2020.Recommanded Product: 60025-09-4 This article mentions the following:

In the title compound, C₁₀H₁₃N₅, the piperidine ring adopts a chair conformation with the exocyclic N-C bond in an axial orientation, and the dihedral angle between the mean planes of piperidine and pyrimidine rings is 49.57 (11)°. A short intramol. C-H···N contact generates an S(7) ring. In the crystal, N-H···N hydrogen bonds link the mols. into (100) sheets and a weak aromatic π-π stacking interaction is observed [centroid-centroid separation = 3.5559 (11) Å] between inversion-related pyrimidine rings. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Recommanded Product: 60025-09-4).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Recommanded Product: 60025-09-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A biomimetic catalytic aerobic functionalization of phenols was written by Esguerra, Kenneth Virgel N.;Fall, Yacoub;Lumb, Jean-Philip. And the article was included in Angewandte Chemie, International Edition in 2014.HPLC of Formula: 5351-07-5 This article mentions the following:

A biomimetic approach that converts phenolic C-H bonds into C-O, C-N, and C-S bonds at the sole expense of reducing O₂ to water (H₂O) was reported. This method hinges on a regio- and chemoselective Cu-catalyzed aerobic oxygenation to provide orthoquinones. Orthoquinones are versatile intermediates, whose direct catalytic aerobic synthesis from phenols enables a mild and efficient means of synthesizing polyfunctional aromatic rings. In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5HPLC of Formula: 5351-07-5).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.HPLC of Formula: 5351-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Targeting the K_v11.1 (hERG) channel with allosteric modulators. Synthesis and biological evaluation of three novel series of LUF7346 derivatives was written by van Veldhoven, Jacobus P. D.;Campostrini, Giulia;van Gessel, Constantijn J. E.;Ward-van Oostwaard, Dorien;Liu, Rongfang;Mummery, Christine L.;Bellin, Milena;IJzerman, Adriaan P.. And the article was included in European Journal of Medicinal Chemistry in 2021.COA of Formula: C8H8N2O This article mentions the following:

Three novel series of substituted benzophenones for their allosteric modulation of the human Kv11.1 (hERG) channel were synthesized and evaluated. Effects of this is compared with reference compound LUF7346 previously shown to shorten the action potential of cardiomyocytes derived from human stem cells. Most compounds behaved as neg. allosteric modulators (NAMs) of [3H]dofetilide binding to the channel. Compound III [R = 2-Cl; R¹ = CH₂cPr; X= Y = C] was the most potent amongst all ligands, remarkably reducing the affinity of dofetilide in competitive displacement assays. One of the other II [R = H; X = N] tested in a second radioligand binding set-up, displayed unusual displacement characteristics with a pseudo-Hill coefficient significantly distinct from unity, further indicative of its allosteric effects on the channel. Some compounds were evaluated in a more physiol. relevant context in beating cardiomyocytes derived from human induced pluripotent stem cells. Surprisingly, the compounds tested showed effects quite different from the reference NAM LUF7346. For instance, compound I [R = 3-Me] prolonged, rather than shortened, the field potential duration, while it did not influence this parameter when the field potential was already prolonged by dofetilide. In subsequent patch clamp studies on HEK293 cells expressing the hERG channel the compounds behaved as channel blockers. In conclusion, new allosteric modulators of the hERG channel were successfully synthesized and identified . Unexpectedly, their effects differed from the reference compound in functional assays on hERG-HEK293 cells and human cardiomyocytes, to the extent that the compounds behaved as stand-alone channel blockers. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1COA of Formula: C8H8N2O).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. COA of Formula: C8H8N2O

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Structure-Based Design, Synthesis, and Biological Evaluation of Imidazo[4,5-b]Pyridin-2-one-Based p38 MAP Kinase Inhibitors: Part 2 was written by Kaieda, Akira;Takahashi, Masashi;Fukuda, Hiromi;Okamoto, Rei;Morimoto, Shinji;Gotoh, Masayuki;Miyazaki, Takahiro;Hori, Yuri;Unno, Satoko;Kawamoto, Tomohiro;Tanaka, Toshimasa;Itono, Sachiko;Takagi, Terufumi;Sugimoto, Hiroshi;Okada, Kengo;Lane, Weston;Sang, Bi-Ching;Saikatendu, Kumar;Matsunaga, Shinichiro;Miwatashi, Seiji. And the article was included in ChemMedChem in 2019.Application In Synthesis of 3-Amino-4-methylbenzonitrile This article mentions the following:

We identified novel potent inhibitors of p38 mitogen-activated protein (MAP) kinase using a structure-based design strategy, beginning with lead compound, 3-(butan-2-yl)-6-(2,4-difluoroanilino)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1). To enhance the inhibitory activity of 1 against production of tumor necrosis factor-α (TNF-α) in human whole blood (hWB) cell assays, we designed and synthesized hybrid compounds in which the imidazo[4,5-b]pyridin-2-one core was successfully linked with the p-methylbenzamide fragment. Among the compounds evaluated, 3-(3-tert-butyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl)-4-methyl-N-(1-methyl-1H-pyrazol-3-yl)benzamide (25) exhibited potent p38 inhibition, superior suppression of TNF-α production in hWB cells, and also significant in vivo efficacy in a rat model of collagen-induced arthritis (CIA). In this paper, we report the discovery of potent, selective, and orally bioavailable imidazo[4,5-b]pyridin-2-one-based p38 MAP kinase inhibitors. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Application In Synthesis of 3-Amino-4-methylbenzonitrile).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Application In Synthesis of 3-Amino-4-methylbenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Optical activity in βγ-unsaturated ketones. Part 2. Effect of the magnitude and energy of the electric transition dipole moment in the aromatic groups in 1- and 1,5-substituted 9,10-ethano-9,10-dihydroanthracen-11-one derivatives was written by Hagishita, Sanji;Kuriyama, Kaoru. And the article was included in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1978.COA of Formula: C11H11N This article mentions the following:

Optically active dihydroanthracene derivatives I (e.g., Z = H₂, O; R = CO₂H, R¹ = H; R = R¹ = CONH₂) were prepared from the Diels-Alder adduct of II (R = H, CO₂Me) and CH₂:C(OAc)CN. Alteration of the substituents of I changed the magnitude of the transition dipole moment and the transition energy in the aromatic chromophore, and the optical activity depended on the transition dipole-moment magnitude. In the experiment, the researchers used many compounds, for example, 5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0COA of Formula: C11H11N).

5,6,7,8-Tetrahydronaphthalene-1-carbonitrile (cas: 29809-13-0) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. COA of Formula: C11H11N

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of electrogenerated triphenylmethyl anion as a base for alkylation of arylacetic esters and arylacetonitriles and isomerization of allylbenzenes was written by Suzuki, Shohei;Kato, Mitsuko;Nakajima, Shoichi. And the article was included in Canadian Journal of Chemistry in 1994.Application In Synthesis of 2-(4-Methoxyphenyl)-2-methylpropanenitrile This article mentions the following:

Phenylacetic esters and phenylacetonitriles were alkylated with alkyl halides, at the position α to an ester or nitrile, either at room temperature (20°) or at -78°, by making use of electrogenerated triphenylmethyl anion (trityl anion). For example, regioselective alkylation of benzeneacetates gave α-alkylbenzeneacetates I (X = H, MeO; R¹ = alkyl; R² = Me, Et). Double-bond isomerization of allylbenzenes was also effectively accomplished using this electrogenerated base (EGB). In the experiment, the researchers used many compounds, for example, 2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5Application In Synthesis of 2-(4-Methoxyphenyl)-2-methylpropanenitrile).

2-(4-Methoxyphenyl)-2-methylpropanenitrile (cas: 5351-07-5) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Application In Synthesis of 2-(4-Methoxyphenyl)-2-methylpropanenitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Direct one-step conversion of alcohols into nitriles was written by Davis, Roman;Untch, Karl G.. And the article was included in Journal of Organic Chemistry in 1981.Reference of 4435-14-7 This article mentions the following:

Primary, secondary, and tertiary alcs. (10 compounds) are converted into the corresponding nitriles by treatment with two equivalent of NaCN-Me₃SiCl and a catalytic amount of NaI in DMF-CH₃CN. The reactions are complete in 2-8 h. Except for cyclohexanol, the yields range from 75-98%. Evidence is presented which demonstrates that S_N2 and S_N1 processes are obtained and a common bis-silyloxonium intermediate is suggested. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Reference of 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Reference of 4435-14-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Co-Monomer Control of Carbon Nitride Semiconductors to Optimize Hydrogen Evolution with Visible Light was written by Zhang, Jinshui;Zhang, Guigang;Chen, Xiufang;Lin, Sen;Moehlmann, Lennart;Dolega, Grzegorz;Lipner, Grzegorz;Antonietti, Markus;Blechert, Siegfried;Wang, Xinchen. And the article was included in Angewandte Chemie, International Edition in 2012.Product Details of 55406-13-8 This article mentions the following:

Herein, we advance a strategy by employing a variety of new monomer building blocks with the desired compositions and electronic structures for chem. incorporation into the conjugated polymeric network of g-C₃N₄. Most precursors of carbon nitride polymers contain cyano groups, amino groups, or both, with the simplest case being cyanamide, which can undergo multiple thermal condensations to form stable aromatic carbon nitrides based on tri-s-triazine subunits. Therefore, we synthesized organic mols. bearing amino and/or cyano functionalities to integrate them directly into the carbon nitride polymers. This design may allow ample choice of organic anchoring groups, being a potentially valuable way to alter the phys. and chem. properties of the resulting heterogeneous organo-catalysts. In the experiment, the researchers used many compounds, for example, 3-Methylthiophene-2-carbonitrile (cas: 55406-13-8Product Details of 55406-13-8).

3-Methylthiophene-2-carbonitrile (cas: 55406-13-8) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Product Details of 55406-13-8

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

An Old Story in the Parallel Synthesis World: An Approach to Hydantoin Libraries was written by Bogolubsky, Andrey V.;Moroz, Yurii S.;Savych, Olena;Pipko, Sergey;Konovets, Angelika;Platonov, Maxim O.;Vasylchenko, Oleksandr V.;Hurmach, Vasyl V.;Grygorenko, Oleksandr O.. And the article was included in ACS Combinatorial Science in 2018.Quality Control of 3-Amino-4-methylbenzonitrile This article mentions the following:

An approach to the parallel synthesis of hydantoin libraries by reaction of in situ generated 2,2,2-trifluoroethylcarbamates and α-amino esters was developed. To demonstrate utility of the method, a library of 1158 hydantoins designed according to the lead-likeness criteria (MW 200-350, cLogP 1-3) was prepared The success rate of the method was analyzed as a function of physicochem. parameters of the products, and it was found that the method can be considered as a tool for lead-oriented synthesis. A hydantoin-bearing submicromolar primary hit acting as an Aurora kinase A inhibitor was discovered with a combination of rational design, parallel synthesis using the procedures developed, in silico and in vitro screenings. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Quality Control of 3-Amino-4-methylbenzonitrile).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Quality Control of 3-Amino-4-methylbenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reaction of substituted benzenes and chloral. VII. Reaction of ο-acetotoluidide and chloral was written by Yasue, Masaichi;Takai, Yoshiharu;Yoshizawa, Shigeru. And the article was included in Yakugaku Zasshi in 1957.HPLC of Formula: 60710-80-7 This article mentions the following:

O-Acetotoluidide (30 g.), 33 g. CCl₃CH(OH)₂, and 100 ml. concentrated H₂SO₄ heated 20 hrs. at 50-60°, the product poured over ice, let stand overnight, the precipitate filtered off, washed with H₂O, refluxed with 700 ml. H₂O, cooled, the precipitate filtered off, and extracted with C₆H₆ gave 12 g. C₆H₆-soluble portion (I) and a small amount of C₆H₆-insoluble portion (II); the above reaction 3 weeks at 10-15° yielded 6.7 g. I and 13.5 g. II (this yielded 0.5 g. substance, m. 158-65°); the reaction 10 days at 20° yielded 13 g. I and 3.5 g. II. I (12 g.) in 80 ml. AcOH treated portionwise with 15 g. Zn, heated 4 hrs. on an H₂O bath, the solution filtered while hot, the filtrate neutralized with NH₄OH, the solution concentrated in vacuo, and the residue extracted with C₆H₆ gave 2.1 g. 2,5-Me(Cl₂CHCH₂)C₆H₃NHAc (III), needles, m. 155.5-6° (EtOH). III (1.7 g.) in 30 ml. EtOH and 0.5 g. NaOH in 10 ml. EtOH refluxed 1 hr., the EtOH removed by heating with 1 g. NH₄Cl and 2 ml. H₂O, and the residue extracted with C₆H₆ gave 1.2 g. 2,5-Me(ClCH:CH)C₆H₃NHAc (IV), needles, m. 173-3.5° (EtOH). IV (0.9 g.) in 50 ml. Me₂CO treated dropwise with 1.5 g. KMnO₄ in 40 ml. H₂O, let stand 2 hrs., the solution decolorized with Na₂SO₃ and concentrated, the residue acidified with 10% H₂SO₄, and the product recrystallized from EtOH gave 4,3-Me(AcNH)C₆H₃CO₂H (V), needles, m. 277°. II (13 g.), 80 ml. AcOH, and 15 g. Zn was heated 4 hrs.; the product in a small amount of EtOH gave 0.1 g. insoluble [4,3-Me(AcNH)C₆H₃]₂C₂H₄, needles, m. 298°, and the filtrate gave III, m. 156°. 4,3-Me(O₂N)C₆H₃CN (10 g.), 25 g. Sn, and 100 ml. EtOH at 25-45° treated with 70 ml. concentrated H₂SO₄, heated until a clear solution was obtained, the EtOH removed, the residue made alk. with NaOH, and extracted with Et₂O gave 8 g. 4,3-Me(H₂N)C₆H₃CN (VI), m. 76-8°. VI (8 g.) and 15 ml. Ac₂O refluxed 1 hr. and the product diluted with 100 ml. H₂O gave 10 g. 4,3-Me(AcNH)C₆H₃CN (VII), m. 153-4° (EtOH). VII (8 g.), 150 ml. EtOH, 50 ml. 30% H₂O₂, and 4 ml. 10% NaOH let stand overnight, the EtOH removed, and the residue recrystallized from H₂O gave 6 g. 4,3-Me(AcNH)C₆H₃CONH₂ (VIII), columns, m. 185-7°. VIII (4 g.) and 50 ml. concentrated H₂SO₄ at 0° treated portionwise with 2.5 g. NaNO₂, let stand 1 hr. at room temperature, the precipitate filtered off, taken up in 10% Na₂CO₃, the solution filtered, the filtrate acidified with 10% H₂SO₄, and the product recrystallized from 50% EtOH gave 2.5 g. V, needles, m. 278°. V (0.5 g.), 5 ml. AcOH, 5 ml. concentrated HCl, and 2.5 ml. H₂O heated 30 min. on an H₂O bath, the product made alk. with NH₄OH, evaporated to dryness, and the residue recrystallized from H₂O gave 4,3-Me(H₂N)C₆H₃CO₂H, columns, m. 164°. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7HPLC of Formula: 60710-80-7).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.HPLC of Formula: 60710-80-7

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts